methyl α-aminohexadecanoate hydrochloride | 129850-59-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl α-aminohexadecanoate hydrochloride
• 英文别名: 2-amino-hexadecanoic acid methyl ester; hydrochloride；2-Amino-hexadecansaeure-methylester; Hydrochlorid
• CAS: 129850-59-5
• 化学式: C₁₇H₃₅NO₂*ClH
• 分子量: 321.931
• InChiKey: OKVRNEYVHHUWAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl α-aminohexadecanoate hydrochloride 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid bis-[(1-methoxycarbonyl-pentadecylcarbamoyl)-methyl] ester
  参考文献：
  名称：

  Lipophilic methotrexate conjugates with antitumor activity

  摘要：

  Lipophilic methotrexate (MTX)-lipoamino acid conjugates coupled with amide or ester Linkages (1a-1r) were synthesised. The inhibitory activity of the conjugates was evaluated on bovine Liver DHFR. The in vitro growth inhibitory effect against MTX-sensitive human lymphoblastoid CCRF-CEM cells and an MTX-resistant sub-line (CEM/MTX), which displays defective intracellular transport of MTX, was determined under short-term and continuous (120-h incubation) exposure conditions. The alpha, gamma, or alpha,gamma amide conjugates showed different activity in inhibiting the growth of parent cells. CEM/MTX cells were much less susceptible than CCRF-CEM cells to inhibition by alpha or alpha,gamma-substituted lipoamino acid conjugates, whereas both cell lines were almost equally sensitive to the MTX-gamma conjugates. Although less potent than MTX, they could partially circumvent the impaired transport system. These findings confirm that lipophilic MTX conjugates may be good lead compounds on the drug development for the treatment of some MTX-resistant tumors. Ester-type conjugates displayed an interesting activity against parent CCRF-CEM cells, although they were less potent against the transport-resistant sub-line. Stability studies on these molecules indicated that they are not degraded into MTX in the culture medium, thus suggesting that they are not able to over-cross cell resistance despite of their lipophilicity. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(00)00062-2
• 作为产物：
  描述：

  2-十四烷基-2-乙酰氨基丙二酸二乙酯 在 盐酸 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl α-aminohexadecanoate hydrochloride
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：

文献信息

• Lipoamino Acid Conjugates of Methotrexate with Antitumor Activity
  作者：Rosario Pignatello、Gerrit Jansen、Ietje Kathmann、Giovanni Puglisi、Istvan Toth

  DOI：10.1021/js970194p

  日期：1998.3

  The synthesis, characterization, and in vitro antitumor activity against a wild and a transport-resistant CCRF-CEM cell line is described for a series of alpha,gamma-bisamide lipoamino acid and oligomer conjugates of methotrexate. The influence of the lipophilicity of the conjugates on the cytotoxicity and the dihydrofolate reductase inhibition was investigated. All compounds were more active than their fatty acid conjugate analogues. Compound 1e with a 12-carbon atom aliphatic side chain showed the highest in vitro activity.